Materials for organic electroluminescence devices

ABSTRACT

The present invention relates to novel materials which can be used in organic electronic devices, in particular electroluminescent devices, and are certain derivatives of fused aromatic systems.

Organic semiconductors are used as functional materials in a number ofdifferent applications which can be ascribed to the electronics industryin the broadest sense. The general structure of organicelectroluminescent devices (OLEDs) is described, for example, in U.S.Pat. No. 4,539,507, U.S. Pat. No. 5,151,629, EP 0676461 and WO 98/27136.

However, these devices still exhibit considerable problems which requireurgent improvement: for example, the operating lifetime is still short,in particular in the case of blue emission, and consequently it hashitherto only been possible to implement simple applicationscommercially Furthermore, the host materials in accordance with theprior art used for blue emitters, which frequently comprise fusedaromatic systems, are often only sparingly soluble in common organicsolvents, which makes their purification during the synthesis, but alsothe cleaning of the plants during production of the organic electronicdevices more difficult.

As closest prior art, mention can be made of the use of various fusedaromatic compounds, in particular anthracene or pyrene derivatives, ashost materials, in particular for blue-emitting electroluminescentdevices. The host material known from the prior art is9,10-bis(2-naphthyl)anthracene (U.S. Pat. No. 5,935,721). Furtheranthracene derivatives which are suitable as host materials aredescribed, for example, in WO 01/076323, in WO 01/021729, in WO04/013073, in WO 04/018588, in WO 03/087023 or in WO 04/018587. Hostmaterials based on aryl-substituted pyrenes and chrysenes are describedin WO 04/016575, which in principle also encompasses correspondinganthracene and phenanthrene derivatives. WO 03/095445 and CN 1362464describe 9,10-bis(1-naphthyl)anthracene derivatives for use in OLEDs.For high-quality applications, however, it is necessary to have improvedhost materials available. Particularly problematical is the poorsolubility of many of the said systems in accordance with the prior art,which makes the preparation, purification and processing of thecompounds more difficult.

The above-mentioned prior art confirms that the host material plays acrucial role in the functioning of organic electroluminescent devices.There thus continues to be a demand for improved materials, inparticular host materials for blue-emitting OLEDs, which result in goodefficiencies and at the same time in long lifetimes in organicelectronic devices and have good solubility. Surprisingly, it has beenfound that organic electronic devices which comprise certain fusedaromatic compounds which are substituted by aryl groups having fusedcycloalkyl groups have significant improvements over the prior art.These materials enable an increase in the lifetime of the organicelectronic device compared with materials in accordance with the priorart. In contrast to the purely aromatic compounds usually used or thosewhich are substituted at most by short open-chain alkyl groups, forexample methyl groups, the compounds according to the invention havehigh solubility in the organic solvents usually used. In contrast tocompounds which are substituted by long open-chain alkyl groups, thecompounds according to the invention can also be sublimed withoutproblems. The present invention therefore relates to these materials andto the use thereof in organic electronic devices.

JP 2005/008600 describes9,10-bis(5,6,7,8-tetrahydro-2-naphthyl)anthracene derivatives as host oras hole-transport compound in organic electronic devices. However, thesecompounds are not suitable for the production of dark-blue-emittingdevices.

The invention relates to compounds of the formula (1)

where the following applies to the symbols and indices used:

-   Ar¹ is on each occurrence, identically or differently, a fused aryl    or heteroaryl group having at least 14 aromatic ring atoms, which    may be substituted by one or more radicals R;-   X is on each occurrence, identically or differently, a group of the    formula (2) or formula (3)

-   -   where the dashed bond denotes the link from Ar² or Q to Ar¹;

-   Y is on each occurrence, identically or differently, X, an Ar³ group    or an N(Ar³)₂ group, where the two Ar³ radicals may also be bonded    to one another by a single bond or an O, S, N(R) or C(R)₂ group;

-   Ar² is on each occurrence, identically or differently, an aryl or    heteroaryl group, which may be substituted by one or more radicals R    and to which the group Q is bonded, with the proviso that either the    group Q or a radical R other than H is bonded in the ortho-position    to the Ar²—Ar¹ bond;

-   Ar³ is on each occurrence, identically or differently, an aromatic    or heteroaromatic ring system, which may be substituted by one or    more radicals R;

-   Q is on each occurrence, identically or differently, a linear,    branched or cyclic alkylene or alkylidene group which forms two    bonds to Ar² or one bond to the adjacent Ar¹ and one bond to Ar² and    thereby forms a further ring system; Q here contains 1 to 20 C atoms    and may be substituted by R¹, and one or more non-adjacent C atoms    may also be replaced by N—R¹, O, S, O—CO—O, CO—O, —CR¹═CR¹— or    —C≡C—, and one or more H atoms may be replaced by F, Cl, Br, I or    CN;

-   R is on each occurrence, identically or differently, H, D, F, Cl,    Br, I, CN, a straight-chain alkyl or alkoxy chain having 1 to 40 C    atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 C    atoms, each of which may be substituted by R¹ and in which one or    more non-adjacent C atoms may be replaced by N—R¹, O, S, O—CO—O,    CO—O, —CR¹═CR¹— or —C≡C— and in which one or more H atoms may be    replaced by F, Cl, Br, I or CN, or an aromatic or heteroaromatic    ring system having 5 to aromatic ring atoms, which may also be    substituted by one or more radicals R¹, or a combination of two,    three or four of these systems; two or more radicals R here may also    form a further mono- or polycyclic, aliphatic or aromatic ring    system with one another;

-   R¹ is on each occurrence, identically or differently, H or a    hydrocarbon radical having 1 to 20 C atoms, which may be aliphatic    or aromatic or a combination of aliphatic and aromatic and in which    one or more H atoms may be replaced by F;

-   m is on each occurrence 0 or 1;

-   p is on each occurrence 0, 1 or 2;    with the exception of the following compound;

The compound of the formula (1) preferably has a glass transitiontemperature T_(g) of greater than 70° C., particularly preferablygreater than 100° C., very particularly preferably greater than 130° C.

For the purposes of this invention, the ortho-position is taken to meanthe 1,2-position on benzene or other aromatic compounds, i.e. positionson two directly adjacent C atoms of aromatic compounds.

For the purposes of this invention, an aryl group contains 6 to 30 Catoms; for the purposes of this invention, a heteroaryl group contains 2to 30 C atoms and at least one hetero atom, with the proviso that thetotal number of C atoms and hetero atoms is at least 5. The hetero atomsare preferably selected from N, O and/or S. An aryl group or heteroarylgroup here is taken to mean either a simple aromatic ring, i.e. benzene,or a simple heteroaromatic ring, for example pyridine, pyrimidine,thiophene, etc., or a fused aryl or heteroaryl group in the sense of thefollowing definition.

For the purposes of this invention, an aromatic ring system contains 6to 40 C atoms in the ring system. For the purposes of this invention, aheteroaromatic ring system contains 2 to 40 C atoms and at least onehetero atom in the ring system, with the proviso that the total numberof C atoms and hetero atoms is at least 5. The hetero atoms arepreferably selected from N, O and/or S. For the purposes of thisinvention, an aromatic or heteroaromatic ring system is intended to meana system which does not necessarily contain only aryl or heteroarylgroups, but in which, in addition, a plurality of aryl or heteroarylgroups may be interrupted by a short, non-aromatic unit (less than 10%of the atoms other than H, preferably less than 5% of the atoms otherthan H), such as, for example, an sp³-hybridised C, N or O atom. Thus,for example, systems such as 9,9′-spirobifluorene, 9,9-diarylfluorene,triarylamine, diaryl ethers, etc., should also be taken to mean aromaticring systems for the purposes of this invention. Part of the aromatic orheteroaromatic ring system here may also be a fused group in the senseof the following definition.

For the purposes of this invention, a fused aryl group is taken to meana ring system having 10 to 40 aromatic ring atoms in which at least twoaromatic rings are “fused” to one another, i.e. have at least one commonedge and a common aromatic π-electron system. For the purposes of thisinvention, a fused heteroaryl group is taken to mean a ring systemhaving 8 to 40 aromatic ring atoms in which at least two aromatic orheteroaromatic rings, at least one of which is heteroaromatic, are fusedto one another. These ring systems may be substituted by R orunsubstituted. Examples of fused aromatic or heteroaromatic ring systemsare naphthalene, quinoline, benzothiophene, anthracene, phenanthrene,phenanthroline, pyrene, perylene, chrysene, acridine, etc., whilebiphenyl, for example, does not represent a fused aryl group since thereis no common edge between the two ring systems therein. Fluorene, forexample, likewise does not represent a fused aromatic ring system sincethe two phenyl units therein do not form a common aromatic ring system.

For the purposes of the present invention, a C₁- to C₄₀-alkyl group, inwhich, in addition, individual H atoms or CH₂ groups may be substitutedby the above-mentioned groups, is particularly preferably taken to meanthe radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl,n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl,2-ethylhexyl, trifluoro methyl, pentafluoroethyl, 2,2,2-trifluoroethyl,ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl,cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl,propynyl, butynyl, pentynyl, hexynyl or octynyl. A C₁- to C₄₀-alkoxygroup is particularly preferably taken to mean methoxy, ethoxy,n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or2-methyl-butoxy. An aromatic or heteroaromatic ring system having 5-30aromatic ring atoms, which may also in each case be substituted by theabove-mentioned radicals R and which may be linked to the aromatic orhetero-aromatic system via any desired positions, is taken to mean, inparticular, groups derived from benzene, naphthalene, anthracene,phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene,pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene,fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene,tetrahydropyrene, cis- or trans-indenofluorene, furan, benzofuran,isobenzofuran, dibenzofuran, thiophene, benzothiophene,isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole,carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine,benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,phenothiazine, phenoxazine, pyrazole, indazole, imidazole,benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole,pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole,naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole,1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine,benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene,2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene,4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine,phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline,phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole,1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole,1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole,1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine,tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine,purine, pteridine, indolizine and benzothiadiazole.

Depending on whether Q forms a ring system with Ar¹ or with Ar², thestructures of the formula (4) or formula (5) thus arise for p=0 orformula (6) for p greater than or equal to 1:

The fused aryl or heteroaryl group Ar¹ preferably contains three, four,five or six aromatic or heteroaromatic units, which are in each casefused to one another via one or more common edges and thus form a commonaromatic system and may be substituted by R or unsubstituted. The fusedaryl or heteroaryl group Ar¹ particularly preferably contains three,four or five aromatic or heteroaromatic units, in particular three orfour aromatic or heteroaromatic units, which are in each case fused toone another via one or more common edges and thus form a common aromaticsystem and may be substituted by R or unsubstituted. The aromatic andheteroaromatic units fused to one another are very particularlypreferably selected from benzene, pyridine, pyrimidine, pyrazine andpyridazine, each of which may be substituted by R or unsubstituted, inparticular benzene.

The fused aryl or heteroaryl groups Ar¹ are particularly preferablyselected from the group consisting of anthracene, acridine,phenanthrene, phenanthroline, pyrene, naphthacene, chrysene, pentacene,phenanthroline and perylene, each of which may optionally be substitutedby R. The substitution by R may be appropriate in order to obtaincompounds with better solubility or in order to adjust the electronicproperties. The fused aryl or heteroaryl groups Ar¹ are particularlypreferably selected from the group consisting of anthracene,phenanthrene, pyrene or perylene, in particular anthracene and pyrene,each of which may optionally be substituted by R. The linking of theunits X and Y to the anthracene preferably takes place here via the2,6-position or via the 9,10-position, particularly preferably via the9,10-position. The linking to the pyrene preferably takes place via the1,6-, 1,8-, 1,3- or 2,7-position, particularly preferably via the 1,6-or 2,7-position. The linking to the phenanthrene preferably takes placevia the 2,7-, 3,6-, 2,9- or 2,10-position, particularly preferably viathe 2,7- or 3,6-position. The linking to the perylene preferably takesplace via the 3,9-, 3,10-, 3,8- or 2,8-position, particularly preferablyvia the 3,9- or 3,10-position. The linking to the phenanthrolinepreferably takes place via the 2,9- or 3,8-position.

Particular preference is given to the following structures of theformulae (7) to (12)

where X and Y have the same meaning as described above, and where theanthracene or phenanthrene or pyrene units may be substituted by one ormore radicals R.

If Y represents an Ar³ group, preferred Ar³ groups, identically ordifferently on each occurrence, are aromatic or heteroaromatic ringsystems having 5 to 20 aromatic ring atoms, particularly preferablyhaving 5 to 16 aromatic ring atoms, very particularly preferably having6 to 14 aromatic ring atoms. The Ar³ groups here may in each case besubstituted by R or unsubstituted. Particular preference is given toaromatic ring systems which contain no aromatic heteroatoms. Examples ofparticularly preferred Ar³ groups are phenyl, 1-naphthyl, 2-naphthyl,2-phenanthrenyl, 3-phenanthrenyl, 9-anthryl, ortho-biphenyl,meta-biphenyl and para-biphenyl, each of which may be substituted by oneor more radicals R.

If Y represents an N(Ar³)₂ group, Y then preferably stands for a groupof the formula (13) or formula (14)

where R and m have the meaning indicated above, and furthermore:

-   A stands for a single bond, O, S, N(R) or C(R)₂;-   Ar³ is, identically or differently on each occurrence, an aryl or    heteroaryl group having 5 to 20 aromatic ring atoms, which may be    substituted by one or more radicals R, preferably an aryl or    heteroaryl group having 6 to 14 aromatic ring atoms, which may be    substituted by one or more radicals R, particularly preferably    phenyl, 1-naphthyl or 2-naphthyl, each of which may be substituted    by one or more radicals R.

The radicals R here are preferably H, F or an alkyl group having 1 to 4C atoms.

Preferred Ar² groups, identically or differently on each occurrence, arearyl or heteroaryl groups having 5 to 16 aromatic ring atoms, preferablyhaving 6 to 10 aromatic ring atoms, particularly preferably phenyl,naphthyl or anthryl, very particularly preferably phenyl.

Particularly preferred structures of the formula (2) are the followingstructures of the formulae (15) to (20)

where Q has the same meaning as described above, and where the phenyl ornaphthyl or anthryl unit may in each case also be substituted by R; thedashed bond here denotes the link to the Ar¹ unit.

In a preferred embodiment of the invention, the groups X and Y areselected to be identical.

In a further preferred embodiment of the invention, the groups X and Yare selected to be different, and Y stands for a fused aryl orheteroaryl group 30 having 9 to 20 aromatic ring atoms or for an N(Ar³)₂group.

Q is preferably a linear alkylene chain having 2 to 15 C atoms or abranched or cyclic alkylene group having 3 to 15 C atoms, each of whichmay be substituted by R¹ and in which one or more non-adjacent C atomsmay also be replaced by N—R¹, O or S and one or more H atoms may bereplaced by F or CN. Q is particularly preferably a linear, branched orcyclic alkylene chain having 3 to 10 C atoms, which may be substitutedby R¹ and in which one or more non-adjacent C atoms may be replaced byN—R¹ or O and one or more H atoms may be replaced by F.

Q is preferably bonded to the ortho-position of Ar², where theortho-position relates to the linking of Ar² to Ar¹.

The preferred ring size formed by Q depends on whether the further ringsystem is formed with Ar¹ or with Ar². If Q forms a ring system withAr¹, the ring size of the ring system formed by Ar¹, Ar² and Q ispreferably a 6-membered ring, a 7-membered ring or an 8-membered ring,particularly preferably a 7-membered ring or an 8-membered ring. Theserelatively large ring systems are preferred since the Ar² group isthereby rotated with respect to Ar¹ and thus results in dark-blueabsorption and emission. If Q forms a ring system with Ar², the ringsystem formed by Ar² and Q preferably contains 3 to 8 ring atoms; itparticularly preferably contains 4, 5, 6 or 7 ring atoms, veryparticularly preferably 5, 6 or 7 ring atoms.

Q preferably forms a ring system with Ar². In this case, the two linksof Q to Ar² may take place in different positions of Ar², for example inthe 1,2-position (ortho), in the 1,3-position (meta) or in the1,4-position (para). The two links of Q to Ar² preferably take place inthe ortho-position to one another.

In a particularly preferred embodiment of the invention, Q is selectedin such a way that it either contains no benzylic protons, i.e. noprotons on the C atom linked directly to Ar², or that a bridgehead Catom is linked directly to Ar². This preference is due to the higherreactivity of benzylic protons, which may result in undesired sidereactions in the OLED. Benzylic protons can be avoided by introducingsubstituents into the corresponding positions or by using branchedalkylene chains for Q. Benzylic protons can furthermore be avoided bynot directly bonding a carbon atom, but instead, for example, an oxygenatom to Ar². The preference of bridgehead C atoms in the direct link toAr² is due to the fact that protons optionally bonded to the bridgeheadhave very low reactivity and therefore do not have the above-mentioneddisadvantages.

Very particularly preferred groups of the formula (2) are the groups ofthe formulae (21) to (24) shown below

where R has the same meaning as described above, and furthermore:

Z is CR₂, O, S, NR, PR, P(═O)R, SiR₂ or CR₂—CR₂;

n is 1, 2 or 3, preferably 2;the dashed bond here denotes the link to the Ar¹ unit.

Preferred structures of the formulae (21) to (23) are those in which theradical R stands for a group other than H or D.

Preference is furthermore given to compounds of the formula (1) in whichthe index p is equal to 0 or 1; the index p is particularly preferablyequal to 0.

Some compounds of the formula (1) can form atropisomers, i.e. isomerswhich arise due to hindered rotation about the X—Ar¹ and about the Ar¹—Ybond, If the compounds of the formula (1) form atropisomers, theinvention encompasses mixtures both of the two (or where appropriatealso more) different atropisomers and the enriched or pure atropisomersof the compound.

Examples of suitable compounds of the formula (1) are the structures (1)to (98) shown below.

Compounds of the formula (1) can be synthesised by standard methods oforganic chemistry. A standard method which is used for the preparationof similar systems in accordance with the prior art and which can alsobe used for the synthesis of the compounds according to the invention isthe Suzuki coupling between an aromatic halide and an aromatic boronicacid derivative. Thus, for example, the Suzuki coupling of a boronicacid derivative of group X to a dihalide of a fused aromatic group Ar¹gives symmetrically substituted compounds of the formula (1).Asymmetrically substituted compounds of the formula (1) can besynthesised by, for example, firstly carrying out the coupling between Xand Ar¹, then halogenating Ar¹ and coupling the product to a boronicacid derivative of Y. It is equally possible firstly to carry out thecoupling between Ar¹ and Y, then to halogenate Ar¹ and to couple theproduct to a boronic acid derivative of X. Other coupling reactions arelikewise possible, for example Stille, Negishi, Sonogashira and Heckcoupling, Grignard cross-coupling, etc. The starting compound X in theform of the halide can be prepared, inter alia, by direct bromination ofthe corresponding cycloalkylaromatic compounds, such as, for example,1,2,3,4-tetrahydronaphthalene, to give5-bromo-1,2,3,4-tetrahydronaphthalene (Ranu et al., SyntheticCommunications 1992, 22(8), 1095) or of indane to give4-bromo-2,3-dihydro-1H-indane (Kostermans et al., J. Org. Chem. 1988,53(19), 4531) or also by cycloadditions from intermediate arynes, as,for example, in the case of5-bromo-1,4-methano-1,2,3,4-tetrahydronaphthalene, which can be obtainedfrom 1,3-dibromo-2-fluorobenzene and cyclopentadiene (Tanida et al., J.Am. Chem. Soc. 1956, 87(21), 4794). The aryne can be prepared in situ bymethods known to the person skilled in the art of organic synthesis. Afurther method for the preparation of the aryne in situ consists in theconversion of a corresponding ortho-halophenol into the correspondingtriflate, which can then be reacted with magnesium to give the aryne andscavenged using a diene.

Some general access routes to the classes of compound according to theinvention are shown in the following schemes:

Preparation of the Substituents X: Tetrahydronaphth-1-yls

1,4-Methano-1,2,3,4-tetrahydronaphth-1-yls

Coupling to Give Structures (1), (13) and (42) Shown Above: Structure(1):

Structure (13);

Structure (42):

If the compounds of the formula (1) are able to form atropisomers, itmay be sensible to separate the atropisomers in order to have availablepure compounds for use in organic electronic devices. The way in whichatropisomers can be separated is described in detail, for example, inthe unpublished application EP 04026402.0. For example,recrystallisation, chromatography or fractional sublimation are suitablefor this purpose.

Suitably functionalised compounds of the formula (1), in particularbrominated compounds, such as, for example, the structures (51) to (56),(87) and (88) shown above, can also be used for incorporation intopolymers.

The invention therefore furthermore relates to conjugated, partiallyconjugated or non-conjugated polymers, oligomers or dendrimerscomprising recurring units of the formula (1). At least one radical Rhere on units of the formula (1) represents a bond to the polymer. Asfurther recurring units, the polymers comprise, for example, fluorenes(for example in accordance with EP 842208 or WO 00/22026),spirobifluorenes (for example in accordance with EP 707020, EP 894107,WO 031020790 or EP 04028865.6), para-phenylenes (for example inaccordance with WO 92/18552), dihydrophenanthrenes (for example inaccordance with WO 05/014689), phenanthrenes (for example in accordancewith WO 05/104264), indenofluorenes (for example in accordance with WO04/041901 or WO 041113412), carbazoles (for example in accordance withWO 04/070772 or WO 04/113468), anthracenes, naphthalenes (for example inaccordance with EP 04030093.1), triarylamines, metal complexes orthiophenes (for example in accordance with EP 1028136) or also aplurality of these units. Homopolymers of the recurring units of theformula (1) are also possible.

The invention furthermore relates to mixtures comprising at least onecompound of the formula (1) and one or more dopants. The dopants arepreferably selected from the class of aromatic anthracenamines, aromaticanthracenediamines, aromatic pyrenamines, aromatic pyrenediamines,monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines,styrylphosphines, styryl ethers and arylamines. An aromaticanthracenamine is taken to mean a compound in which a diarylamino groupis bonded directly to an anthracene group, preferably in the 9-position.An aromatic anthracenediamine is taken to mean a compound in which twodiarylamino groups are bonded directly to an anthracene group,preferably in the 9,10-positions Aromatic pyrenamines and pyrenediaminesare defined analogously. A monostyrylamine is taken to mean a compoundwhich contains one styryl group and at least one, preferably aromatic,amine. A distyrylamine is taken to mean a compound which contains twostyryl groups and at least one, preferably aromatic, amine. Atristyrylamine is taken to mean a compound which contains three styrylgroups and at least one, preferably aromatic, amine. A tetrastyrylamineis taken to mean a compound which contains four styryl groups and atleast one, preferably aromatic, amine. Corresponding phosphines andethers are defined analogously to the amines. For the purposes of thisinvention, an arylamine or an aromatic amine is taken to mean a compoundwhich contains three aromatic or heteroaromatic ring systems bondeddirectly to the nitrogen. The styryl groups are particularly preferablystilbenes, which may also be further substituted. Preferred dopants areselected from the classes of the tristilbenamines, the aromaticstilbenediamines, the anthracenediamines and the pyrenediamines,Particularly preferred dopants are selected from the class of thetristyrylamines and the stilbenediamines. Examples of such dopants aresubstituted or unsubstituted tristilbenamines or the dopants describedin WO 06/000388 and in the unpublished patent applications EP 04028407.7and EP 05001891.0.

The invention furthermore relates to the use of compounds of the formula(1) or corresponding polymers in organic electronic devices.

The present invention furthermore relates to organic electronic devicescomprising anode, cathode and at least one organic layer which comprisesat least one compound of the formula (1) or a corresponding polymer.

The organic electronic device is preferably selected from the group ofelectronic devices consisting of organic and polymeric light-emittingdiodes (OLEDs, PLEDs), organic field-effect transistors (O-FETs),organic thin-film transistors (O-TFTs), organic light-emittingtransistors (O-LETs), organic integrated circuits (O-ICs), organic solarcells (O-SCs), organic field-quench devices (O-FQDs), light-emittingelectrochemical cells (LECs), organic photoreceptors and organic laserdiodes (O-lasers). Preference is given to organic and polymericlight-emitting diodes.

The organic electronic device comprises one or more organic layers, ofwhich at least one layer comprises at least one compound of the formula(1). If it is an organic electroluminescent device, at least one organiclayer is an emission layer. In organic transistors, at least one organiclayer is a charge-transport layer. In organic electroluminescentdevices, further layers may also be present in addition to the emittinglayer. These can be, for example: hole-injection layer, hole-transportlayer, charge-blocking layer, electron-transport layer and/orelectron-injection layer. However, it should be pointed out at thispoint that each of these layers does not necessarily have to be present.

The compounds of the formula (1) can be used as host material fordopants which emit light from the singlet state or from a state ofhigher spin multiplicity (for example the triplet state), as dopant, ashole-transport material, as electron-transport material or ashole-blocking material. The preferred use of compounds of the formula(1) depends on the substituents present, in particular on the group Y.

If the group Y stands for a group X or for an aromatic or heteroaromaticring system, in particular for a fused aryl group, the compound of theformula (1) is preferably used as host material together with a dopantwhich emits light from the singlet state. These compounds are alsosuitable for use in an electron-transport layer and/or in ahole-blocking layer. Preferred dopants are selected from the group ofaromatic anthracenamines, aromatic anthracenediamines, aromaticpyrenamines, aromatic pyrenediamines, monostyrylamines, distyrylamines,tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers andarylamines, where these classes of compound are as defined above.

If the group Y stands for an N(Ar³)₂ group, the compound of the formula(1) is preferably employed as emitting compound (emitting dopant). It isthen preferably employed in combination with a host material. Suitableas host material are, for example, the above-mentioned compoundsaccording to the invention, but also other host materials as usuallyused in accordance with the prior art. These are, in particular,oligoarylenes (for example 2, 2′,7,7′-tetraphenylspirobifluorene inaccordance with EP 676461 or dinaphthylanthracene), in particularoligoarylenes containing fused aromatic groups, oligoarylenevinylenes(for example DPVBi or spiro-DPVBi in accordance with EP 676461),polypodal metal complexes (for example in accordance with WO 04/081017),hole-conducting compounds (for example in accordance with WO 04/058911),electron-conducting compounds, in particular ketones, phosphine oxides,sulfoxides, etc. (for example in accordance with WO 05/084081 or WO05/084082), atropisomers (for example in accordance with the unpublishedapplication EP 04026402.0) or boronic acid derivatives (for example inaccordance with the unpublished application EP 05009643.7). Particularlypreferred host materials are selected from the classes of oligoarylenescontaining naphthalene, anthracene and/or pyrene or atropisomers ofthese compounds, oligoarylenevinylenes, ketones, phosphine oxides andsulfoxides. Very particularly preferred host materials are selected fromthe classes of oligoarylenes containing anthracene and/or pyrene oratropisomers of these compounds, phosphine oxides and sulfoxides.

The proportion of the dopant in the mixture of the emitting layer isbetween 0.1 and 99.0% by weight, preferably between 0.5 and 50.0% byweight, particularly preferably between 1.0 and 20.0% by weight, inparticular between 1.0 and 10.0% by weight. Correspondingly, theproportion of the host material in the emitting layer is between 1.0 and99.9% by weight, preferably between 50.0 and 99.5% by weight,particularly preferably between 80.0 and 99.0% by weight, in particularbetween 90.0 and 99.0% by weight.

If the group Y stands for an N(Ar³)₂ group, the compound of the formula(1) can also be employed as hole-transport compound. It is thenpreferably employed in a hole-transport layer or in a hole-injectionlayer. For the purposes of this invention, a hole-injection layer is alayer which is directly adjacent to the anode. For the purposes of thisinvention, a hole-transport layer is a layer which is between ahole-injection layer or also another hole-transport layer and anemitting layer.

Preference is furthermore given to an organic electronic device which ischaracterised in that one or more layers are coated by a sublimationprocess, in which the materials are vapour-deposited in vacuumsublimation units at a pressure below 10⁻⁵ mbar, preferably below 10⁻⁶mbar, particularly preferably below 10⁻⁷ mbar.

Preference is likewise given to an organic electronic device which ischaracterised in that one or more layers are coated by the OVPD (organicvapour phase deposition) process or with the aid of carrier-gassublimation, in which the materials are generally applied at a pressurebetween 10⁻⁵ mbar and 1 bar.

Preference is furthermore given to an organic electronic device which ischaracterised in that one or more layers are produced from solution,such as, for example, by spin coating, or by any desired printingprocess, such as, for example, screen printing, flexographic printing oroffset printing, but particularly preferably LITI (light induced thermalimaging, thermal transfer printing) or ink-jet printing.

The emitting devices described above have the following surprisingadvantages over the prior art:

-   1. The stability of corresponding devices is greater compared with    systems in accordance with the prior art, which is particularly    evident from a longer lifetime.-   2. In contrast to compounds used to date, which were in some cases    very difficult to purify due to their poor solubility, the compounds    of the formula (1) are readily soluble and therefore easier to    purify and also easier to process from solution.-   3. In contrast to compounds used to date which have no substituents    on X in the ortho-position to the link to Ar¹, the compounds of the    formula (1) according to the invention can also be employed as host    materials for dark-blue emitters, while similar materials in    accordance with the prior art, such as, for example, in accordance    with JP 2005/008600, are only suitable for pale-blue emitters.-   4. The use of the compounds according to the invention in OLEDs    results in greater efficiency of the light emission.

The invention is explained in greater detail by the following examples,without wishing to be restricted thereby.

EXAMPLES

The following syntheses are carried out under a protective-gasatmosphere, unless indicated otherwise. The starting materials can bepurchased from ALDRICH or ABCR(tris(dibenzylideneacetone)dipaliadium(0),2-dicyclohexylphosphino-2,6-dimethoxybiphenyl, 9,10-dibromoanthracene,1,6-dibromopyrene, 1,3,6,8-tetrabromopyrene, inorganics, solvents).5-Bromo-1,2,3,4-tetrahydro-1,4-methanonaphthalene is prepared by themethod of Tanida et al., J. Am. Chem. Soc. 1965, 87(21), 4794, and5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-8-methylnaphthalene isprepared analogously to6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene by the methodof Garipova et al., Tetrahedron 2005, 61(20), 4755.5-Bromo-1,2,3,4-tetrahydronaphthalene is synthesised as described inSynthetic Communications 1992, 22(8), 1095-1099.(5,6,7,8-Tetrahydro-1-naphthyl)boronic acid is synthesised as describedin US 2002/019527.

Example 1 9,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracenea) 1,2,3,4-Tetrahydro-1,4-methanonaphthalene-5-boronic Acid

100 ml (250 mmol) of n-butyllithium (2.5M in hexane) are added dropwiseto a solution, cooled to −78° C., of 44.6 g (200 mmol) of5-bromo-1,2,3,4-tetrahydro-1,4-methanonaphthalene in 500 ml of THF. Thereaction mixture is stirred at −78° C. for 1 h, and a mixture of 33.5 ml(300 mmol) of trimethyl borate in 50 ml of THF is then added rapidly.After warming to −10° C., the mixture is hydrolysed using 10 ml of 2.5Mhydrochloric acid, and 500 ml of methyl tert-butyl ether are then added.The organic phase is separated off, washed with water, dried over sodiumsulfate and evaporated to dryness. The residue is taken up in 200 ml ofn-heptane, and the colourless solid is filtered off with suction, washedwith n-heptane and dried under reduced pressure. Yield: 24.1 g (128mmol), 64.1% of theory; purity: 98% according to ¹H-NMR.

b) 9,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracene

915 my (1 mmol) of tris(dibenzylidenacetone)dipalladium(0) and 821 mg (2mmol) of 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl are added to asuspension of 16.8 g (50 mmol) of 9,10-dibromoanthracene, 21.6 g (115mol) of 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-boronic acid and66.9 g (315 mmol) of tripotassium phosphate in 400 ml of anhydroustoluene, and the mixture is refluxed for 16 h. After the reactionmixture has been cooled, 400 ml of water are added, and the precipitateis filtered off with suction, washed three times with 200 ml of watereach time, washed three times with 200 ml of ethanol each time, driedunder reduced pressure and subsequently chromatographed on silica gel(eluent heptane/toluene 8:2, v/v, column temperature 500C). Sublimation:p=1×10⁻⁵ mbar, 300° C. Yield: 13.1 g (28 mmol), 56.6% of theory; purity:99.5% according to ¹H-NMR (including all isomers).

Example 2 1,6-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)pyrene

Preparation analogous to Example 1. Instead of 9,10-dibromoanthracene,18.0 g (50 mmol) of 1,6-dibromopyrene are used. Purification byrecrystallisation from NMP. Yield: 16.8 g (34.5 mmol), 69.0% of theory;purity: 99.9% according to ¹H-NMR.

Example 3 9,10-Bis(5,6,7,8-tetrahydro-1-naphthyl)anthracene

688 mg (2.26 mmol) of tri-o-tolylphosphine and then 84 mg (0.37 mmol) ofpalladium(II) acetate are added to a vigorously stirred, degassedsuspension of 12.7 g (37.7 mmol) of 9,10-dibromoanthracene, 17.2 g (97.7mmol) of (5,6,7,8-tetrahydro-1-naphthyl)boronic acid and 26.6 g (126mmol) of tripotassium phosphate in a mixture of 230 ml of toluene, 115ml of dioxane and 170 ml of water, and the mixture is refluxed for 60 h.After cooling, the organic phase is separated off, washed three timeswith 200 ml of water and once with 200 ml of saturated, aqueous sodiumchloride solution, dried over magnesium sulfate and evaporated todryness under reduced pressure. The grey residue obtained in this way isrecrystallised from dioxane. The deposited crystals are filtered offwith suction, washed with 50 ml of ethanol and dried under reducedpressure; yield: 7.5 g, 45% having a purity of 99.8% according to HPLC.

The following compounds are prepared analogously to Examples 1 to 3:

Example Aryl bromide Product 4

5

6

7

8

9

10

11

12

Example 139,10-Bis(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-8-methylnaphth-5-yl)anthracenea) 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-8-methylnaphthalene-5-boronicAcid

Preparation analogous to Example 1a. Instead of5-bromo-1,2,3,4-tetrahydro-1,4-methanonaphthalene, 56.2 g (200 mmol) of5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-8-methyl naphthalene areemployed. Yield: 36.5 g (148 mmol), 74.1% of theory; purity: 98%according to ¹H-NMR.

b)9,10-Bis(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-8-methylnaphthalen-5-yl)anthracene

Preparation analogous to Example 1b. Instead of 21.6 g (115 mmol) of1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-boronic acid, 36.9 g (150mmol) of1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-8-methylnaphthalene-5-boronicacid are used. Sublimation: p 1×10⁻⁵ mbar, 310° C. Yield: 15.9 g (27.5mmol), 54.9% of theory; purity: 99.9% according to ¹H-NMR,atropisomerically pure.

The following compounds are prepared analogously to Example 13:

Example Aryl bromide Product 14

15

16

17

18

19

20

21

Example 22 Production of Fluorescent OLEDs Comprising Host MaterialsH1-H6 According to the Invention for Blue-Electroluminescent OLEDs

OLEDs are produced by a general process as described in WO 04/058911,which is adapted in individual cases to the particular circumstances(for example layer-thickness variation in order to achieve optimumefficiency or colour).

The results for various OLEDs are presented in Examples 23 to 42 below.The basic structure and the materials used (apart from the emittinglayer) are identical in the examples for better comparability. OLEDshaving the following structure are produced analogously to theabove-mentioned general process:

Hole-injection layer (HIL) 20 nm PEDOT (spin-coated from water;purchased from H.C. Starck, Goslar, Germany; poly(3,4-ethylenedioxy-2,5-thio-phene)) Hole-transport layer 20 nm2,2′,7,7′-tetrakis(di-para-tolylamino)- (HTL1) spiro-9,9′-bifluorene(vapour-deposited) Hole-transport layer 20 nm NPB(N-naphthyl-N-phenyl-4,4′-di- (HTL2) aminobiphenyl) Emission layer (EML)30 nm layer of H1 to H7 as host material doped with x % (see table) ofdopant E1 (vapour-deposited, synthesised as described in WO 06/000388)Electron conductor (ETC) 20 nm (vapour-deposited; AlQ₃ purchased fromSynTec; tris(quinolinolato)- aluminium (III)) Cathode 1 nm LiF, 150 nmAl on top.

The OLEDs can also be produced without PEDOT as hole-injection layer. Inthis case, the HTL1 then serves as hole-injection layer. Comparableresults are obtained with these OLEDs.

These OLEDs are characterised by standard methods; for this purpose, theelectroluminescence spectra, the efficiency (measured in cd/A) and thepower efficiency (measured in Im/W) as a function of the brightness,calculated from current/voltage/brightness characteristic lines (IULcharacteristic lines), are determined.

The host materials used (H1 to H7) and the emitter material used (E1)are listed below. The host H7 serves as comparative material inaccordance with the prior art.

Emitter E1

Host H1

Host H2

Host H3

Host H4

Host H5

Host H6

Host H7

Table 1 shows the results for some OLEDs (Examples 23 to 42). As can beseen from the examples in Table 1 OLEDs comprising the host materialsaccording to the invention (H1 to H6) in combination with emitter E1exhibit efficient blue emission. Greater efficiency and a darker bluecolour are obtained here than with di-1-naphthylanthracene in accordancewith the prior art.

TABLE 1 Voltage (V) Max. efficiency at Example EML (cd/A) 1000 cd/m² CIE23 H1 7.7 6.3 x = 0.16; 5% E1 y = 0.25 24 H1 6.9 6.5 x = 0.16; 3% E1 y =0.21 25 H2 7.2 6.2 x = 0.16; 3% E1 y = 0.21 26 H2 8.1 6.1 x = 0.16; 5%E1 y = 0.25 27 H2 7.8 6.0 x = 0.16; 7% E1 y = 0.27 28 H3 7.7 6.2 x =0.16; 3% E1 y = 0.22 29 H3 8.2 6.0 x = 0.16; 5% E1 y = 0.25 30 H3 7.56.3 x = 0.16; 7% E1 y = 0.26 31 H4 7.1 6.4 x = 0.16; 3% E1 y = 0.22 32H4 8.1 6.0 x = 0.16; 5% E1 y = 0.25 33 H4 7.2 6.2 x = 0.16; 7% E1 y =0.29 34 H5 7.5 6.2 x = 0.16; 3% E1 y = 0.22 35 H5 8.3 6.1 x = 0.16; 5%E1 y = 0.25 36 H5 7.5 6.1 x = 0.16; 7% E1 y = 0.28 37 H6 7.7 6.6 x =0.16; 3% E1 y = 0.29 38 H6 8.5 6.5 x = 0.16; 5% E1 y = 0.32 39 H6 7.06.1 x = 0.16; 7% E1 y = 0.33 40 H7 6.3 6.9 x = 0.16; (comparison) 3% E1y = 0.23 41 H7 7.8 6.1 x = 0.16; (comparison) 5% E1 y = 0.28 42 H7 6.56.0 x = 0.16; (comparison) 7% E1 y = 0.30

Example 43

Examples of OLEDs which comprise emitters according to the invention areshown below. Emitters E2 and E3 according to the invention used arelisted below:

Emitter 2 E2

Emitter 3 E3

Table 2 shows the results for some OLEDs (Examples 44 to 50). As can beseen from the examples in Table 2, OLEDs comprising emitter E2 or E3according to the invention exhibit good efficiencies and good bluecolour coordinates. Furthermore, emitters E2 and E3 according to theinvention have greater thermal stability than emitter E1 in accordancewith the prior art.

TABLE 2 Max. Voltage (V) efficiency at Example EML (cd/A) 1000 cd/m² CIE44 H7 6.5 6.5 x = 0.16; 5% E2 y = 0.20 45 H7 6.6 6.4 x = 0.16; 5% E3 y =0.18 46 H7 6.8 6.3 x = 0.16; 7% E3 y = 0.21 47 H2 6.8 6.4 x = 0.15; 5%E2 y = 0.20 48 H2 6.9 6.5 x = 0.16; 5% E3 y = 0.20 49 H5 6.7 6.4 x =0.16; 5% E2 y = 0.21 50 H5 6.8 6.3 x = 0.16; 5% E3 y = 0.20

1-24. (canceled)
 25. A compound of formula (1)

wherein Ar¹ is, identically or differently on each occurrence, a fusedaryl or heteroaryl group having at least 14 aromatic ring atomsoptionally substituted by one or more R; X is, identically ordifferently on each occurrence, a group of formula (2) or (3)

wherein the dashed bond is a link from Ar² or Q to Ar¹; Y is,identically or differently on each occurrence, X; an Ar³ group; or anN(Ar³)₂ group, wherein the two Ar³ radicals are optionally bonded to oneanother by a single bond or via an O, S, N(R), or C(R)₂ group; Ar² is,identically or differently on each occurrence, an aryl or heteroarylgroup optionally substituted by one or more R and to which a group Q isbonded, with the proviso that either the group Q or an R other than H isbonded in the orthoposition to the Ar¹—Ar² bond; Ar³ is, identically ordifferently on each occurrence, an aromatic or heteroaromatic ringsystem optionally substituted by one or more R; Q is, identically ordifferently on each occurrence, a linear, branched, or cyclic alkyleneor alkylidene group which forms two bonds to Ar² or one bond to Ar¹ andone bond to Ar² and thereby defining a further ring system; wherein Qhas up to 20 C atoms optionally substituted by R¹, wherein one or morenon-adjacent C atoms are optionally replaced by N—R¹, O, S, O—C—O, CO—O,—CR¹≡CR¹—, or —C≡C—, and one or more H atoms are optionally replaced byF, Cl, Br, I, or CN; R is, identically or differently on eachoccurrence, H, F, Cl, Br, I, CN, a straight-chain alkyl or alkoxy chainhaving up to 40 C atoms, or a branched or cyclic alkyl or alkoxy grouphaving 3 to 40 C atoms, wherein said straight-chain alkyl or alkoxychain or said branched or cyclic alkyl or alkoxy group are optionallysubstituted by R¹, wherein one or more non-adjacent C atoms areoptionally replaced by N—R¹, O, S, O—CO—O, CO—O, —CR¹═CR¹—, or —CO≡C—,and wherein one or more H atoms are optionally replaced by F, Cl, Br, I,CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromaticring atoms optionally substituted by one or more R¹, or a combination oftwo, three or four of these systems; and wherein two or more R hereoptionally define a further mono- or polycyclic, aliphatic, or aromaticring system with one another; R¹ is, identically or differently on eachoccurrence, H or a hydrocarbon radical having up to 20 C atoms, whereinsaid hydrocarbon radical is optionally aliphatic or aromatic or acombination of aliphatic and aromatic, and wherein one or more H atomsare optionally replaced by F; m is, on each occurrence, 0 or 1; p is, oneach occurrence, 0, 1, or 2; with the proviso that the followingcompound is excluded as a compound of formula (1):


26. The compound of claim 25, wherein Ar¹ contains three, four, five, orsix aromatic or heteroaromatic units, which are in each case fused toone another via one or more common edges and are optionally substitutedby R.
 27. The compound of claim 26, wherein Ar¹ is selected from thegroup consisting of anthracene, acridine, phenanthrene, phenanthroline,pyrene, naphthacene, chrysene, pentacene, phenanthroline, and perylene,each of which is optionally substituted by R.
 28. The compound of claim25, wherein the compound of formula (1) is selected from the groupconsisting of structures of formula (7), (8), (9), (10), (11), and (12):

wherein the anthracene, phenanthrene, and pyrene units are optionallysubstituted by one or more R.
 29. The compound of claim 25, wherein Ar³is, identically or differently on each occurrence, an aromatic orheteroaromatic ring system having 5 to 20 aromatic ring atoms optionallysubstituted by R.
 30. The compound of claim 25, wherein Ar², is,identically or differently on each occurrence, an aryl or heteroarylgroup having 5 to 16 aromatic ring atoms optionally substituted by R.31. The compound of claim 25, wherein Q is a linear, branched, or cyclicalkylene chain having 2 to 15 C atoms optionally substituted by R¹,wherein one or more non-adjacent C atoms are optionally replaced byN—R¹, O, or S and one or more H atoms are optionally replaced by F orCN.
 32. The compound of claim 25, wherein Q is bonded to theortho-position of Ar², where said ortho-position is relative to the linkbetween Ar² and Ar¹.
 33. The compound of claim 25, wherein Q defines a6-, 7-, or 8-membered ring system together with Ar¹ and Ar² or defines a3-, 4-, 5-, 6-, 7-, or 8-membered ring system together with Ar².
 34. Thecompound of claim 25, wherein the structures of formula (2) are selectedfrom the group consisting of the structures of formula (15), (16), (17),(18), (19), and (20):

wherein the phenyl, naphthyl, or anthryl unit are in each caseoptionally substituted by R and wherein the dashed bond is the link tothe Ar¹ unit.
 35. The compound of claim 34, wherein the structures offormula (2) are selected from the group consisting of the structures offormula (21), (22), (23), and (24):

wherein Z is CR₂, O, S, NR, PR, P(═O)R, SiR₂, or CR₂—CR₂; n is 1, 2, or3; and the dashed bond is the link to the Ar¹ unit.
 36. The compound ofclaim 25, wherein Q defines a ring system with Ar².
 37. The compound ofclaim 25, wherein Q contains no benzylic protons or a bridgehead C atomis linked directly to Ar².
 38. The compound of claim 25, wherein p is 0or
 1. 39. The compound of claim 25, wherein said compounds are selectedfrom structures (1) to (98):


40. A conjugated, partially conjugated, or non-conjugated polymer,oligomer, or dendrimer comprising recurring units of the compound ofclaim 25, wherein at least one R is a bond to the polymer.
 41. Theconjugated, partially conjugated, or non-conjugated polymer, oligomer,or dendrimer of claim 40, wherein said conjugated, partially conjugated,or non-conjugated polymer, oligomer, or dendrimer further comprisesrecurring units selected from the group consisting of fluorenes,spirobifluorenes, para-phenylenes, dihydrophenanthrenes, phenanthrenes,indenofluorenes, carbazoles, anthracenes, naphthalenes, triarylamines,metal complexes, thiophenes, and combinations thereof or wherein saidconjugated, partially conjugated, or non-conjugated polymer, oligomer,or dendrimer is a homopolymer.
 42. A mixture comprising at least onecompound of claim 25 and one or more dopants.
 43. The mixture of claim42, wherein said dopants are selected from the group consisting ofaromatic anthracenamines, aromatic anthracenediamines, aromaticpyrenamines, aromatic pyrene-diamines, monostyrylamines, distyrylamines,tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers, andarylamines.
 44. An organic electronic device comprising a compound ofclaim
 25. 45. An organic electronic device comprising anode, cathode,and at least one organic layer which comprises at least one compound ofclaim
 25. 46. The organic electronic device of claim 45, wherein saiddevice is selected from the group consisting of organic and polymericlight-emitting diodes, organic field-effect transistors, organicthin-film transistors, organic light-emitting transistors, organicintegrated circuits, organic solar cells, organic field-quench devices,light-emitting electrochemical cells, organic photoreceptors, andorganic laser diodes.
 47. The organic electronic device of claim 45,wherein said device is an organic electroluminescent device comprisingan emitting layer and one or more further layers selected from the groupconsisting of hole-injection layers, hole-transport layers,charge-blocking layers, electron-transport layers, electron-injectionlayers, combinations thereof.
 48. The organic electronic device of claim45, wherein said device is an organic electroluminescent device andwherein said at least one compound is a host material for dopants whichemit light from the singlet state or from a state of higher spinmultiplicity, a dopant, a hole-transport material, an electron-transportmaterial, or a hole-blocking material.